Sodium Bicarbonate → HCID 59825057, compound

HRID 886623Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:15]=2)[N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:9]=1.[NH2:34][C:35]1[C:40]([CH:41]([OH:47])[C:42]([N:44]([CH3:46])[CH3:45])=[O:43])=[CH:39][C:38](Br)=[CH:37][N:36]=1.C(=O)(O)[O-].[Na+]>C(#N)C.O1CCCC1>[NH2:34][C:35]1[C:40]([CH:41]([OH:47])[C:42]([N:44]([CH3:45])[CH3:46])=[O:43])=[CH:39][C:38]([C:14]2[CH:15]=[C:16]3[C:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[F:1])=[CH:9][N:10]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:31])[CH3:33])[C:11]3=[N:12][CH:13]=2)=[CH:37][N:36]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3-(2-Fluoro-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (289 mg, 0.617 mmol), 2-(2-amino-5-bromo-pyridin-3-yl)-2-hydroxy-N,N-dimethyl-acetamide (168.5 mg, 0.617 mmol) and dichloro[1,1′-bis(diphenyl-phosphino)ferrocene]palladium(II) dichloromethane adduct (25 mg, 0.031 mmol) were combined in 1:1 acetonitrile/tetrahydrofuran (4 mL) under nitrogen. Saturated sodium bicarbonate was added (4 mL), also under nitrogen, and the mixture was capped and heated for 18 h at 80° C. After cooling, the aqueous layer was removed and the organic layer was purified by silica gel chromatography using DCM and MeoH as eluent to afford 2-{2-Amino-5-[3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-3-yl}-2-hydroxy-N,N-dimethyl-acetamide (130 mg, 39.3%). MS: m/z 536 (M+H+).

Workup

customalso under nitrogen, and the mixture was capped
temperatureAfter cooling
customthe aqueous layer was removed
customthe organic layer was purified by silica gel chromatography

Sources & evidence

ORD record: ord-b4493816a532402f83a9d5a49fd261c8
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242280B2

Reaction notes

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